Multicomponent synthesis of spiro 1,3,4‐thiadiazolines with anticancer activity by using deep eutectic solvent under microwave irradiation

Castro, Aleff Cruz de; Andrade, Isadora Maria Gouvêa; Coelho, Maísa Cavalcanti; Costa, Daniel Pereira da; Moreira, Dayse das Neves; Maia, Rachel Azevedo; Lima, Gesiane da Silva; Santos, Glauber Eduardo de Oliveira; Vaz, Boniek G.; Militão, Gardênia Carmen Gadelha; Silva, Paulo Bruno Norberto da; Vasconcellos, Mário Luiz Araújo de Almeida; Lima-Júnior, Cláudio Gabriel

doi:10.1002/jhet.4591

Cited by 9 publications

(1 citation statement)

References 55 publications

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“…The results of these studies contribute to the development of novel drugs with targeted biological activities, potentially leading to therapeutic advances. Microwave irradiation (MWI) was investigated as a means of introducing acetyl functionality to the OH group [ 31 , 32 , 33 ]. Acetic acid and acetyl chloride were used as a cheaper acetylating reagent in place of acetic anhydride, which has been banned in some countries due to safety concerns.…”

Section: Introductionmentioning

confidence: 99%

Exploration of Binding Affinities of a 3β,6β-Diacetoxy-5α-cholestan-5-ol with Human Serum Albumin: Insights from Synthesis, Characterization, Crystal Structure, Antioxidant and Molecular Docking

Alam

2023

Molecules

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The present study describes the synthesis, characterization, and in vitro molecular interactions of a steroid 3β,6β-diacetoxy-5α-cholestan-5-ol. Through conventional and solid-state methods, a cholestane derivative was successfully synthesized, and a variety of analytical techniques were employed to confirm its identity, including high-resolution mass spectrometry (HRMS), Fourier transforms infrared (FT-IR), nuclear magnetic resonance (NMR), elemental analysis, and X-ray single-crystal diffraction. Optimizing the geometry of the steroid was undertaken using density functional theory (DFT), and the results showed great concordance with the data from the experiments. Fluorescence spectral methods and ultraviolet–vis absorption titration were employed to study the in vitro molecular interaction of the steroid regarding human serum albumin (HSA). The Stern-Volmer, modified Stern-Volmer, and thermodynamic parameters’ findings showed that steroids had a significant binding affinity to HSA and were further investigated by molecular docking studies to understand the participation of active amino acids in forming non-bonding interactions with steroids. Fluorescence studies have shown that compound 3 interacts with human serum albumin (HSA) through a static quenching mechanism. The binding affinity of compound 3 for HSA was found to be 3.18 × 104 mol−1, and the Gibbs free energy change (ΔG) for the binding reaction was −9.86 kcal mol−1 at 298 K. This indicates that the binding of compound 3 to HSA is thermodynamically favorable. The thermodynamic parameters as well as the binding score obtained from molecular docking at various Sudlow’s sites was −8.2, −8.5, and −8.6 kcal/mol for Sites I, II, and III, respectively, supporting the system’s spontaneity. Aside from its structural properties, the steroid demonstrated noteworthy antioxidant activity, as evidenced by its IC50 value of 58.5 μM, which is comparable to that of ascorbic acid. The findings presented here contribute to a better understanding of the pharmacodynamics of steroids.

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Section: Introductionmentioning

confidence: 99%

Exploration of Binding Affinities of a 3β,6β-Diacetoxy-5α-cholestan-5-ol with Human Serum Albumin: Insights from Synthesis, Characterization, Crystal Structure, Antioxidant and Molecular Docking

Alam

2023

Molecules

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Recent Advances in the Multicomponent Synthesis of Heterocycles using Thiosemicarbazide

Javahershenas,

Han,

Kazemi

et al. 2024

ChemistrySelect

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This review provides an overview of the recent advances in the synthesis of diverse heterocyclic compounds using thiosemicarbazide as a key building block via multicomponent reactions. Thiosemicarbazide is a versatile reagent that has gained significant attention in organic synthesis due to its ability to participate in diverse multicomponent reactions for the efficient and sustainable construction and assembly of novel bioactive molecules and pharmaceuticals. This review discusses the potential applications and future directions in this rapidly evolving area of research. It provides valuable insights into the innovative approaches for the synthesis of heterocycles using thiosemicarbazide, showcasing its significance in modern organic chemistry research. In summary, this review provides an overview of the current state of the art, highlighting the use of thiosemicarbazide in the synthesis of novel heterocyclic compounds reported between 2015 and early 2024.

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Recent advances in the application of deep eutectic solvents for the synthesis of Spiro heterocyclic scaffolds via multicomponent reactions

Javahershenas

2023

Journal of Molecular Liquids

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Multicomponent synthesis of spiro 1,3,4‐thiadiazolines with anticancer activity by using deep eutectic solvent under microwave irradiation

Cited by 9 publications

References 55 publications

Exploration of Binding Affinities of a 3β,6β-Diacetoxy-5α-cholestan-5-ol with Human Serum Albumin: Insights from Synthesis, Characterization, Crystal Structure, Antioxidant and Molecular Docking

Exploration of Binding Affinities of a 3β,6β-Diacetoxy-5α-cholestan-5-ol with Human Serum Albumin: Insights from Synthesis, Characterization, Crystal Structure, Antioxidant and Molecular Docking

Recent Advances in the Multicomponent Synthesis of Heterocycles using Thiosemicarbazide

Recent advances in the application of deep eutectic solvents for the synthesis of Spiro heterocyclic scaffolds via multicomponent reactions

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